TW448139B - Method of preparing benzyl metal compounds and method of preparing 4-phenyl-1-butenes using the same - Google Patents
Method of preparing benzyl metal compounds and method of preparing 4-phenyl-1-butenes using the same Download PDFInfo
- Publication number
- TW448139B TW448139B TW086107274A TW86107274A TW448139B TW 448139 B TW448139 B TW 448139B TW 086107274 A TW086107274 A TW 086107274A TW 86107274 A TW86107274 A TW 86107274A TW 448139 B TW448139 B TW 448139B
- Authority
- TW
- Taiwan
- Prior art keywords
- patent application
- phenyl
- item
- scope
- manufacturing
- Prior art date
Links
- -1 benzyl metal compounds Chemical class 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 59
- PBGVMIDTGGTBFS-UHFFFAOYSA-N but-3-enylbenzene Chemical class C=CCCC1=CC=CC=C1 PBGVMIDTGGTBFS-UHFFFAOYSA-N 0.000 title claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 114
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 10
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 10
- 230000003197 catalytic effect Effects 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 229910052708 sodium Inorganic materials 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 14
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 239000011591 potassium Substances 0.000 claims description 7
- 150000003335 secondary amines Chemical class 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000002736 metal compounds Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- TZTOGCOAZOYBOG-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3CC12)C=CC=C Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)C=CC=C TZTOGCOAZOYBOG-UHFFFAOYSA-N 0.000 claims 1
- NRWGWVPBBBHHSR-UHFFFAOYSA-N [Au].[Os] Chemical compound [Au].[Os] NRWGWVPBBBHHSR-UHFFFAOYSA-N 0.000 claims 1
- 239000010953 base metal Substances 0.000 claims 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N chembl421 Chemical compound C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 claims 1
- 238000001514 detection method Methods 0.000 claims 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 claims 1
- VRAOQOFWZFIOSZ-UHFFFAOYSA-N osmium potassium Chemical compound [K].[Os] VRAOQOFWZFIOSZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 35
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 18
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 11
- MRIWRLGWLMRJIW-UHFFFAOYSA-N benzyl(trimethyl)silane Chemical compound C[Si](C)(C)CC1=CC=CC=C1 MRIWRLGWLMRJIW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 7
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229940043279 diisopropylamine Drugs 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 210000005069 ears Anatomy 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- OWMHBKYAOYHOQK-UHFFFAOYSA-N sodium;methanidylbenzene Chemical compound [Na+].[CH2-]C1=CC=CC=C1 OWMHBKYAOYHOQK-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- YNXURHRFIMQACJ-UHFFFAOYSA-N lithium;methanidylbenzene Chemical compound [Li+].[CH2-]C1=CC=CC=C1 YNXURHRFIMQACJ-UHFFFAOYSA-N 0.000 description 3
- 125000006178 methyl benzyl group Chemical group 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 235000015170 shellfish Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MOZVGCZFICTLDL-UHFFFAOYSA-N [Na].[Na]c1ccccc1 Chemical compound [Na].[Na]c1ccccc1 MOZVGCZFICTLDL-UHFFFAOYSA-N 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- MWOBKFYERIDQSZ-UHFFFAOYSA-N benzene;sodium Chemical compound [Na].C1=CC=CC=C1 MWOBKFYERIDQSZ-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LMJDMESPXVAQQY-UHFFFAOYSA-N n-propan-2-ylhexan-1-amine Chemical compound CCCCCCNC(C)C LMJDMESPXVAQQY-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- ZAJKEDQTROWDDD-HWKANZROSA-N (e)-1-chloro-2-methylbut-2-ene Chemical compound C\C=C(/C)CCl ZAJKEDQTROWDDD-HWKANZROSA-N 0.000 description 1
- KIJVFSLXNWLMOW-VOTSOKGWSA-N (e)-1-chlorooct-2-ene Chemical compound CCCCC\C=C\CCl KIJVFSLXNWLMOW-VOTSOKGWSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- KTHUKEZOIFYPEH-UHFFFAOYSA-N 1-benzylnaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 KTHUKEZOIFYPEH-UHFFFAOYSA-N 0.000 description 1
- CVTAWSUBQIZWCS-UHFFFAOYSA-N 1-bromo-4-methoxy-2-methylbut-2-ene Chemical compound COCC=C(C)CBr CVTAWSUBQIZWCS-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 1
- ZEBFPAXSQXIPNF-UHFFFAOYSA-N 2,5-dimethylpyrrolidine Chemical compound CC1CCC(C)N1 ZEBFPAXSQXIPNF-UHFFFAOYSA-N 0.000 description 1
- KQLXLZMCYSIZHH-UHFFFAOYSA-N 2-chloropent-2-ene Chemical compound CCC=C(C)Cl KQLXLZMCYSIZHH-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
- KTFUTPSBLYIILV-UHFFFAOYSA-N 6,6-dichlorohexan-1-amine Chemical compound NCCCCCC(Cl)Cl KTFUTPSBLYIILV-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241001330002 Bambuseae Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- YXOLAZRVSSWPPT-UHFFFAOYSA-N Morin Chemical compound OC1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 YXOLAZRVSSWPPT-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010033109 Ototoxicity Diseases 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 229910052778 Plutonium Inorganic materials 0.000 description 1
- XXWDKWAUNILFEM-UHFFFAOYSA-N S.[Au+3] Chemical compound S.[Au+3] XXWDKWAUNILFEM-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- WHFYAUZAZWJFCQ-UHFFFAOYSA-N [Mg].[Mg].[Au] Chemical compound [Mg].[Mg].[Au] WHFYAUZAZWJFCQ-UHFFFAOYSA-N 0.000 description 1
- UNKQVRFPUYCEJA-UHFFFAOYSA-N [Zn]CC1=CC=CC=C1 Chemical compound [Zn]CC1=CC=CC=C1 UNKQVRFPUYCEJA-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- VQQWQBZZASEJOQ-UHFFFAOYSA-N argon arsane Chemical group [Ar].[AsH3] VQQWQBZZASEJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- XCTMSCBHFJLFCT-UHFFFAOYSA-N benzyltin Chemical compound [Sn]CC1=CC=CC=C1 XCTMSCBHFJLFCT-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical class CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000010814 metallic waste Substances 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 1
- 235000007708 morin Nutrition 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical compound CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 231100000262 ototoxicity Toxicity 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- SKAFPBSZWJKMPR-UHFFFAOYSA-N phosphanylidenemethanone Chemical class O=C=P SKAFPBSZWJKMPR-UHFFFAOYSA-N 0.000 description 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13660896A JP4040707B2 (ja) | 1996-05-30 | 1996-05-30 | ベンジル金属化合物の製造方法 |
| JP19912896A JPH1045641A (ja) | 1996-07-29 | 1996-07-29 | ４−フェニル−１−ブテン類の製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW448139B true TW448139B (en) | 2001-08-01 |
Family
ID=26470134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW086107274A TW448139B (en) | 1996-05-30 | 1997-05-29 | Method of preparing benzyl metal compounds and method of preparing 4-phenyl-1-butenes using the same |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6024897A (ko) |
| EP (1) | EP0866068B1 (ko) |
| KR (1) | KR100494401B1 (ko) |
| DE (1) | DE69714404T2 (ko) |
| TW (1) | TW448139B (ko) |
| WO (1) | WO1997045433A1 (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019042290A1 (zh) * | 2017-08-28 | 2019-03-07 | 捷开通讯(深圳)有限公司 | 一种移动终端的远程控制方法、移动终端的远程控制系统 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2775787T3 (es) * | 2016-03-31 | 2020-07-28 | Dow Global Technologies Llc | Sistemas catalíticos para polimerización de olefinas y métodos de uso de los mismos |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006187A (en) * | 1971-10-06 | 1977-02-01 | Lithium Corporation Of America | Preparation of aryllithium compounds by metalation |
| JPS5336459B2 (ko) * | 1972-01-14 | 1978-10-03 | ||
| US3953535A (en) * | 1974-08-08 | 1976-04-27 | Teijin Limited | Process for the preparation of alkenylbenzenes |
| US4018840A (en) * | 1974-12-24 | 1977-04-19 | Teijin Limited | Process for preparing alkenylbenzenes |
| JPS5217440A (en) * | 1975-07-31 | 1977-02-09 | Ihara Chem Ind Co Ltd | Process for preparation of phenylacetate |
| JPS5377019A (en) * | 1976-12-16 | 1978-07-08 | Nippon Oil Co Ltd | Preparation of organo-alkali metal compound |
| DE3536929A1 (de) * | 1985-10-17 | 1987-04-23 | Basf Ag | Verfahren zur herstellung von alkenylaromaten |
| JP2815218B2 (ja) * | 1990-04-13 | 1998-10-27 | 三井化学株式会社 | ピリミジンジオン誘導体、およびそれを含有する抗不整脈剤 |
| US5030784A (en) * | 1990-02-26 | 1991-07-09 | Shell Oil Company | Process for converting lower-alkyl substituted aromatic compounds and butadiene to 4-aryl-1-butene or 4-aryl-1-pentene and propylene |
| US5329058A (en) * | 1990-04-25 | 1994-07-12 | Teijin Limied | Process for producing alkenylbenzene |
| US5523504A (en) * | 1993-09-17 | 1996-06-04 | Cosmo Oil Co., Ltd. | Process for manufacturing alkenyl aromatic compounds |
| US5659097A (en) * | 1994-01-20 | 1997-08-19 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a monoalkenyl aromatic hydrocarbon compound |
| JPH09157191A (ja) * | 1995-12-06 | 1997-06-17 | K I Kasei Kk | （ｅ）−スチルベン類の製造方法 |
-
1997
- 1997-05-29 TW TW086107274A patent/TW448139B/zh not_active IP Right Cessation
- 1997-05-29 KR KR10-1998-0700681A patent/KR100494401B1/ko not_active IP Right Cessation
- 1997-05-29 US US09/011,266 patent/US6024897A/en not_active Expired - Fee Related
- 1997-05-29 DE DE69714404T patent/DE69714404T2/de not_active Expired - Lifetime
- 1997-05-29 WO PCT/JP1997/001843 patent/WO1997045433A1/ja active IP Right Grant
- 1997-05-29 EP EP97924267A patent/EP0866068B1/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019042290A1 (zh) * | 2017-08-28 | 2019-03-07 | 捷开通讯(深圳)有限公司 | 一种移动终端的远程控制方法、移动终端的远程控制系统 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0866068A1 (en) | 1998-09-23 |
| EP0866068B1 (en) | 2002-07-31 |
| DE69714404D1 (de) | 2002-09-05 |
| EP0866068A4 (en) | 1999-12-01 |
| WO1997045433A1 (fr) | 1997-12-04 |
| DE69714404T2 (de) | 2003-01-09 |
| KR19990036016A (ko) | 1999-05-25 |
| US6024897A (en) | 2000-02-15 |
| KR100494401B1 (ko) | 2005-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4006095A (en) | Stable hydrocarbon solutions of aluminum hydride | |
| US20030009029A1 (en) | Catalytic titanium (IV) oxide, mediated geminal symmetric dialkylation of carboxamides | |
| TW383309B (en) | Optically active beta-aminoalkoxyborane complex and beta-amionalcohol compound, and process for producing and optically active alcohol compound by using said | |
| TWI245757B (en) | Method for 2-alkyl-2-adamanthyl (meth)acrylate production | |
| TW448139B (en) | Method of preparing benzyl metal compounds and method of preparing 4-phenyl-1-butenes using the same | |
| JPH08253486A (ja) | ペンタフルオロフエニル化合物を製造するための方法 | |
| US7572948B2 (en) | Fulvene purification | |
| JP2711770B2 (ja) | エーテルを含まない有機金属アミド組成物 | |
| JP4040707B2 (ja) | ベンジル金属化合物の製造方法 | |
| JP4022713B2 (ja) | シラン化合物及びその製造方法 | |
| CN110730767B (zh) | 环烷基(三氟甲基)苯的制造方法 | |
| JP2661209B2 (ja) | 含フッ素シラン化合物の製造法 | |
| JP2010001222A (ja) | アルコール類の製造方法 | |
| TWI225857B (en) | Process for producing tertiary alcohol having adamantine skeleton | |
| US6515180B1 (en) | Method for the catalytic, symmetric disubstitution of carboxylic acid amides with grignard reagents | |
| JP2614812B2 (ja) | セサモールの製造法 | |
| JP2864985B2 (ja) | トリ（第２級アルキル）シラン化合物の製造方法 | |
| JP2007022921A (ja) | メチルリチウム溶液およびその製造方法 | |
| TW583187B (en) | Preparation of tris(trimethylsilyl) silylethyl esters | |
| JP2002088092A (ja) | 新規な有機金属錯体及びこれを中間体とした高純度有機金属錯体の合成方法 | |
| JP2012224606A (ja) | ４，４，４−トリフルオロ−１−ブタノールの製造法 | |
| JPS62246540A (ja) | アルコキシカルボン酸の製造方法 | |
| JP2002518360A (ja) | カルボキサアミドの触媒酸化チタン（ｉｖ）誘導性ジェミナル不斉ジアルキル化 | |
| JPH06104659B2 (ja) | １−ドデシルアザシクロヘプタン−２−オンの製造方法 | |
| JPH06172327A (ja) | ２−アセチルピラジンの製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GD4A | Issue of patent certificate for granted invention patent | ||
| MM4A | Annulment or lapse of patent due to non-payment of fees |